Tony Stewart has co-owned a Sprint Cup team for more than four years, and some things still don’t come easy.

Sure, landing sponsorship can be tough or chasing the latest NASCAR rules change.

But for Stewart, the toughest part is when personal feelings make a business decision difficult. That’s why he lets other people deliver the bad news when someone must be released or fired.

“It’s the hardest part for me,” Stewart said. “I let somebody else take care of it. That’s probably one of my weaknesses as an owner, having to go tell somebody that you’re not going to need their services anymore.

“That’s the hard part of it. The hard part for me is you build relationships with these people and friendships with them.”

Stewart, who left Joe Gibbs Racing in 2008 to start Stewart-Haas Racing, said he knows the wives and children of many of his employees.

“It’s hard to make a decision like that that you know is going to alter their family but at the same time you have a family of 200 people that you’re responsible for looking out for,” Stewart said.

Stewart doesn’t just own Stewart-Haas Racing, his three-car Sprint Cup team. He has 13 companies and overall approximately 260 employees. He owns three dirt tracks, the Tony Stewart Racing open-wheel teams, a communications agency that has several clients in addition to himself, and he a radio-controlled car company.

He even owns a trucking company.

“The trucking company has been the one that I didn’t know how much it was going to grow,” Stewart said. “We started with four trucks and we’re up to 50 trucks now. So it was one that I didn’t think would grow as big as it has and we’re still planning an expansion.

“That’s one that probably has caught me off-guard more than anything.”

Stewart spoke last week to members of the Martinsville Speedway business community to talk about his work as a businessman.

He said the key is to have some involvement in every company and have checks and balances so he doesn’t spend all the money. His chief financial officer and executive vice president must agree with him on all major decisions.

“If all three of us don’t agree, we don’t do it,” Stewart said.

Stewart talked mostly about owning the three-car Cup organization, which includes teams for Ryan Newman and Danica Patrick in addition to his own No. 14 team.

“Everything for the most part over five years (of SHR) has run pretty smooth so far,” said Stewart, who won the 2011 Chase, his third Cup championship, with his own team. “I don’t think anybody ever says their program is exactly where they want it. The guy that tells you that is the guy that probably is going to get his butt kicked the next year by other teams.

“It’s a constant work in progress. … You’re constantly in that mode of what can we do to make ourselves better than what we already are.”

And sometimes he’s in the mode of wondering what in the world is he doing owning a three-car Cup organization.

“I go to bed sometimes going, ‘What was I thinking?’” said Stewart, who drove for Gibbs for 10 years before moving out on his own. “There’s a lot fewer off-days now than there used to be and a lot more responsibility, especially during the weekend.

“You try to separate it on the weekends and try to just focus on what I do with my car and just be one of the team drivers, but you’re always worried about what’s going on with Ryan’s car and Danica’s car.”

Stewart-Haas has won 17 races since its exception in 2009, 14 of them by Stewart. The organization expanded this year, adding a third car for Patrick.

It also has gone through major sponsorship changes this year, with Bass Pro Shops replacing Office Depot on Stewart’s car and Quicken Loans replacing the U.S. Army for Newman. While Patrick’s car is sponsored primarily by GoDaddy.com, the organization still needs sponsorship for all three teams.

One thing Stewart doesn’t have to focus on is many of the technical details of running a business.

Such as the actual writing of checks and doing his own banking.

“I’ve got three people to do that for me,” Stewart said. “I have not seen a paycheck in over 10 years. When my monthly statement comes, that’s the only way I know exactly how much I make.”

And then Stewart came to a realization.

“At some point I’m going to audit my own people to make sure they’re not getting ready to go to Aruba or somewhere on vacation for the rest of their life,” Stewart quipped.